WO2010114119A1 - Binder composition for non-aqueous secondary battery electrode - Google Patents
Binder composition for non-aqueous secondary battery electrode Download PDFInfo
- Publication number
- WO2010114119A1 WO2010114119A1 PCT/JP2010/056066 JP2010056066W WO2010114119A1 WO 2010114119 A1 WO2010114119 A1 WO 2010114119A1 JP 2010056066 W JP2010056066 W JP 2010056066W WO 2010114119 A1 WO2010114119 A1 WO 2010114119A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- monomer
- ethylenically unsaturated
- secondary battery
- meth
- Prior art date
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- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- MADOXCFISYCULS-UHFFFAOYSA-N octyl 2-sulfanylacetate Chemical compound CCCCCCCCOC(=O)CS MADOXCFISYCULS-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 239000001254 oxidized starch Substances 0.000 description 1
- 235000013808 oxidized starch Nutrition 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- LGYJSPMYALQHBL-UHFFFAOYSA-N pentanedihydrazide Chemical compound NNC(=O)CCCC(=O)NN LGYJSPMYALQHBL-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229930015698 phenylpropene Natural products 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- OGRPJZFGZFQRHZ-UHFFFAOYSA-M sodium;4-octoxy-4-oxo-3-sulfobutanoate Chemical compound [Na+].CCCCCCCCOC(=O)C(S(O)(=O)=O)CC([O-])=O OGRPJZFGZFQRHZ-UHFFFAOYSA-M 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
- H01M4/621—Binders
- H01M4/622—Binders being polymers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F10/02—Ethene
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G11/00—Hybrid capacitors, i.e. capacitors having different positive and negative electrodes; Electric double-layer [EDL] capacitors; Processes for the manufacture thereof or of parts thereof
- H01G11/22—Electrodes
- H01G11/30—Electrodes characterised by their material
- H01G11/32—Carbon-based
- H01G11/38—Carbon pastes or blends; Binders or additives therein
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/13—Electrodes for accumulators with non-aqueous electrolyte, e.g. for lithium-accumulators; Processes of manufacture thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M4/00—Electrodes
- H01M4/02—Electrodes composed of, or comprising, active material
- H01M4/62—Selection of inactive substances as ingredients for active masses, e.g. binders, fillers
- H01M4/621—Binders
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M2220/00—Batteries for particular applications
- H01M2220/30—Batteries in portable systems, e.g. mobile phone, laptop
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/13—Energy storage using capacitors
Definitions
- the present invention relates to a binder composition for a non-aqueous secondary battery electrode excellent in electrolytic solution resistance, binding property, and flexibility. Furthermore, it is related with the binder composition for non-aqueous secondary battery electrodes which can be used suitably for the non-aqueous secondary battery excellent in charging / discharging cycling characteristics and high capacity
- Patent Document 1 as a binder resin, a cross-linking agent is added to an acrylic resin dissolved in a solvent, and the resin and the cross-linking agent are reacted in a heating / compression bonding process at the time of electrode preparation, and then tertiary.
- the active material and the conductive agent are prevented from falling off during battery charging / discharging.
- the three-dimensional crosslinked structure obtained by the heating and pressure bonding conditions at the time of electrode preparation is not sufficiently crosslinked, and crosslinking variation is likely to occur, and sufficient cushioning properties cannot be exhibited.
- the first invention of the present invention is a binder composition for a non-aqueous secondary battery electrode comprising functional group-containing crosslinked resin fine particles, Functional group-containing crosslinked resin fine particles (A) Monomer having one ethylenically unsaturated group and monofunctional or polyfunctional epoxy group in one molecule (a) One ethylenically unsaturated group in one molecule and monofunctional or polyfunctional At least one selected from the group consisting of a monomer (b) having a functional amide group and a monomer (c) having one ethylenically unsaturated group and a monofunctional or polyfunctional hydroxyl group in one molecule.
- the crosslinked structure of the functional group-containing crosslinked resin fine particles in the present invention needs to be crosslinked inside the particles.
- the functional group-containing cross-linked resin fine particles in which the cross-linking inside the particles is appropriately adjusted for the binder composition for a non-aqueous secondary battery electrode it is possible to ensure the resistance to an electrolytic solution.
- cross-linking of particles inter-particle cross-linking
- the electrolyte solution of the cross-linking agent component In some cases, leakage of the electrode and variations in electrode fabrication may occur. For this reason, it is necessary to use a crosslinking agent to such an extent that the electrolyte solution resistance is not impaired.
- Examples of the monomer (a) having one ethylenically unsaturated group and a monofunctional or polyfunctional epoxy group in one molecule include glycidyl (meth) acrylate and 3,4-epoxycyclohexyl (meth) acrylate. Etc.
- Examples of the monomer (c) having one ethylenically unsaturated group and a monofunctional or polyfunctional hydroxyl group in one molecule include 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate. 4-hydroxybutyl (meth) acrylate, 2- (meth) acryloyloxyethyl-2-hydroxyethylphthalic acid, glycerol mono (meth) acrylate, 4-hydroxyvinylbenzene, 1-ethynyl-1-cyclohexanol, allyl Examples include alcohol.
- the functional group (alkoxysilyl group, ethylenically unsaturated group) of the monomer contained in the monomer group (B) is a self-crosslinking reactive functional group, and is mainly used for particle internal cross-linking during particle synthesis. Has the effect of forming. Electrolytic solution resistance can be improved by sufficiently carrying out internal crosslinking of the particles. Therefore, it is possible to obtain crosslinked resin fine particles by using a monomer contained in the monomer group (B). In addition, by sufficiently carrying out particle crosslinking, the resistance to electrolytic solution can be improved.
- Examples of the monomer (n) having one ethylenically unsaturated group and a cyclic structure in one molecule include alicyclic ethylenically unsaturated monomers and aromatic ethylenically unsaturated monomers. It is done.
- Examples of the alicyclic ethylenically unsaturated monomer include cyclohexyl (meth) acrylate and isobornyl (meth) acrylate, and examples of the aromatic ethylenically unsaturated monomer include benzyl (meth) acrylate.
- Phenoxyethyl (meth) acrylate styrene, ⁇ -methylstyrene, 2-methylstyrene, chlorostyrene, allylbenzene, ethynylbenzene and the like.
- Perfluoroalkyl group-containing ethylenically unsaturated compounds such as perfluoroalkyl and alkylenes; polyethylene glycol (meth) acrylate, methoxypolyethylene group Cole (meth) acrylate, ethoxy polyethylene glycol (meth) acrylate, propoxy polyethylene glycol (meth) acrylate, n-butoxy polyethylene glycol (meth) acrylate, n-pentoxypolyethylene glycol (meth) acrylate, phenoxy polyethylene glycol (meth) acrylate , Polypropylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, ethoxypolypropylene glycol (meth) acrylate, propoxypolypropylene glycol (meth) acrylate, n-butoxypolypropylene glycol (meth) acrylate, n-pentoxypolypropylene glycol (meta ) Acry
- Examples of the monomer (m) and the monomer (k) other than the monomer (n) include maleic acid, fumaric acid, itaconic acid, citraconic acid, and alkyl or alkenyl monoesters thereof. , Phthalic acid ⁇ - (meth) acryloxyethyl monoester, isophthalic acid ⁇ - (meth) acryloxyethyl monoester, terephthalic acid ⁇ - (meth) acryloxyethyl monoester, succinic acid ⁇ - (meth) acryloxyethyl Carboxyl group-containing ethylenically unsaturated monomers such as monoesters, acrylic acid, methacrylic acid, crotonic acid and cinnamic acid; Tertiary butyl group-containing ethylenically unsaturated monomers such as tertiary butyl (meth) acrylate; Sulfonic acid group-containing ethylenically unsaturated mono
- keto group-containing ethylenically unsaturated monomer particularly diacetone (meth) acrylamide is a monomer having one ethylenically unsaturated group and a monofunctional or polyfunctional amide group in one molecule as described above ( Since it has the function as b), it is more preferable.
- the cross-linking reaction between the keto group in the functional group-containing cross-linked resin fine particles and the hydrazide group in the polyfunctional hydrazide compound is heat-treated as necessary when preparing the electrode for the purpose of strengthening the cross-linking and adjusting the binder performance. You may go.
- heat treatment is preferably performed at 40 ° C. to 200 ° C.
- the reactive emulsifier having an ethylenically unsaturated group can be further roughly classified into anionic and nonionic nonionic ones.
- anionic reactive emulsifier or a nonionic reactive emulsifier having an ethylenically unsaturated group when used, the dispersed particle size of the copolymer becomes fine and the particle size distribution becomes narrow. Therefore, the binder for a non-aqueous secondary battery electrode When used as an electrolyte, the resistance to electrolytic solution can be improved, which is preferable.
- These anionic reactive emulsifiers or nonionic reactive emulsifiers having an ethylenically unsaturated group may be used singly or in combination.
- Non-reactive emulsifiers can be broadly classified into non-reactive anionic emulsifiers and non-reactive nonionic emulsifiers.
- non-reactive nonionic emulsifiers include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether and polyoxyethylene stearyl ether; polyoxyethylene alkyl such as polyoxyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether Sorbitan monolaurate, sorbitan monostearate, sorbitan higher fatty acid esters such as sorbitan trioleate; polyoxyethylene sorbitan higher fatty acid esters such as polyoxyethylene sorbitan monolaurate; polyoxyethylene monolaurate, Polyoxyethylene higher fatty acid esters such as polyoxyethylene monostearate; oleic acid monoglyceride, stearic acid monog Glycerine higher fatty acid esters such as celite, polyoxyethylene-polyoxypropylene block copolymers, and the like can be exemplified polyoxyethylene distyrenated phenyl ether.
- a water-soluble protective colloid can be used in combination.
- water-soluble protective colloids include polyvinyl alcohols such as partially saponified polyvinyl alcohol, fully saponified polyvinyl alcohol, and modified polyvinyl alcohol; cellulose derivatives such as hydroxyethyl cellulose, hydroxypropyl cellulose, and carboxymethyl cellulose salt; Examples thereof include saccharides, and these can be used alone or in a combination of plural kinds.
- the amount of the water-soluble protective colloid used is 0.1 to 5 parts by weight, more preferably 0.5 to 2 parts by weight per 100 parts by weight of the total amount of ethylenically unsaturated monomers.
- the aqueous medium used in the emulsion polymerization of the functional group-containing crosslinked resin fine particles of the present invention includes water, and a hydrophilic organic solvent can be used as long as the object of the present invention is not impaired.
- the oil-soluble polymerization initiator is not particularly limited, and examples thereof include benzoyl peroxide, tert-butyl peroxybenzoate, tert-butyl hydroperoxide, tert-butyl peroxy (2-ethylhexanoate), and tert-butyl peroxide.
- Organic peroxides such as oxy-3,5,5-trimethylhexanoate and di-tert-butyl peroxide; 2,2′-azobisisobutyronitrile, 2,2′-azobis-2,4- Examples thereof include azobis compounds such as dimethylvaleronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 1,1′-azobiscyclohexane-1-carbonitrile. These can be used alone or in combination of two or more. These polymerization initiators are preferably used in an amount of 0.1 to 10.0 parts by weight with respect to 100 parts by weight of the ethylenically unsaturated monomer.
- reducing agent examples include reducing organic compounds such as metal salts such as ascorbic acid, ersorbic acid, tartaric acid, citric acid, glucose, and formaldehyde sulfoxylate, sodium thiosulfate, sodium sulfite, sodium bisulfite, Examples include reducing inorganic compounds such as sodium bisulfite, ferrous chloride, Rongalite, thiourea dioxide, and the like. These reducing agents are preferably used in an amount of 0.05 to 5.0 parts by weight with respect to 100 parts by weight of the total ethylenically unsaturated monomer.
- the polymerization temperature is not less than the polymerization start temperature of each polymerization initiator.
- the polymerization time is not particularly limited, but is usually 2 to 24 hours.
- ⁇ Other materials used for reaction> sodium acetate, sodium citrate, sodium bicarbonate and the like as a buffering agent, and octyl mercaptan, 2-ethylhexyl thioglycolate, octyl thioglycolate, stearyl mercaptan, lauryl mercaptan as a chain transfer agent
- a suitable amount of mercaptans such as t-dodecyl mercaptan can be used.
- a monomer having an acidic functional group such as a carboxyl group-containing ethylenically unsaturated monomer
- a basic compound before or after the polymerization.
- it can be neutralized with ammonia or alkylamines such as trimethylamine, triethylamine and butylamine; alcohol amines such as 2-dimethylaminoethanol, diethanolamine, triethanolamine and aminomethylpropanol; and a base such as morpholine.
- ammonia or alkylamines such as trimethylamine, triethylamine and butylamine
- alcohol amines such as 2-dimethylaminoethanol, diethanolamine, triethanolamine and aminomethylpropanol
- a base such as morpholine.
- it is a highly volatile base that is highly effective in drying, and preferred bases are aminomethylpropanol and ammonia.
- Measurement of the glass transition temperature by DSC can be performed as follows. About 2 mg of resin obtained by drying the functional group-containing crosslinked resin fine particles is weighed on an aluminum pan, the test container is set on a DSC measurement holder, and the endothermic peak of the chart obtained under a temperature rising condition of 10 ° C./min is obtained. read. The peak temperature at this time is defined as the glass transition temperature of the present invention.
- the average particle size of the functional group-containing crosslinked resin fine particles is preferably 10 to 500 nm, more preferably 30 to 250 nm, from the viewpoint of the binding property of the electrode active material and the stability of the particles. Further, when a large amount of coarse particles exceeding 1 ⁇ m are contained, the stability of the particles is impaired, so that the coarse particles exceeding 1 ⁇ m are preferably at most 5% by weight.
- the average particle diameter in the present invention represents a volume average particle diameter and can be measured by a dynamic light scattering method.
- Measurement of the strength and elongation rate of the coating film with Tensilon can be performed by the following method.
- the functional group-containing crosslinked resin fine particles are dried to prepare a sheet having a thickness of about 0.5 mm.
- the measurement specimen is cut out to 5 mm ⁇ 60 mm, and the film thickness is measured accurately.
- the measurement is performed under a constant temperature and humidity condition of a temperature of 23 ° C. and a humidity of 50%, using a tensile tester [Tensilon manufactured by Orientec Co., Ltd.] with a chuck distance of 20 mm and a tensile speed of 50 mm / min.
- the breaking strength and breaking elongation calculated from the breaking strength and breaking elongation obtained by measurement in consideration of the film thickness are taken as the strength and elongation of the present invention.
- epoxy resins such as bisphenol A-epichlorohydrin type epoxy resins and bisphenol F-epichlorohydrin type epoxy resins, and ethylenically unsaturated monomers containing epoxy group-containing ethylenically unsaturated monomers.
- a radical polymerization resin obtained by polymerizing a saturated monomer is preferred.
- the epoxy resin can be expected to have a synergistic effect of improving the electrolytic solution resistance by having a bisphenol skeleton and improving the adhesion of the current collector by a hydroxyl group contained in the skeleton.
- Uncrosslinked oxazoline group-containing compound examples include 2′-methylenebis (2-oxazoline), 2,2′-ethylenebis (2-oxazoline), and 2,2′-ethylenebis (4-methyl-2-oxazoline).
- Examples of alicyclic polyisocyanates include 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate (also known as IPDI, isophorone diisocyanate), 1,3-cyclopentane diisocyanate, 1,3-cyclohexane diisocyanate, 1, Examples include 4-cyclohexane diisocyanate, methyl-2,4-cyclohexane diisocyanate, methyl-2,6-cyclohexane diisocyanate, 4,4′-methylenebis (cyclohexyl isocyanate), 1,4-bis (isocyanate methyl) cyclohexane, and the like. .
- two or more kinds of compounds (l) in the binder composition can be used in combination.
- an epoxy group derived from the monomer (a) reacts with a carboxyl group to generate a hydroxyl group. It is also possible to form a stronger crosslinked structure by reacting this hydroxyl group with a compound having two or more isocyanate groups.
- ethylene glycol monobutyl ether and propylene glycol monobutyl ether are particularly preferable because they have a high film forming auxiliary effect in a small amount.
- These film forming aids are preferably contained in the binder composition in an amount of 0.5 to 15% by weight.
- Example 1 A reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a refluxing vessel was charged with 40 parts of ion-exchanged water and 0.2 part of Adeka Soap SR-10 (manufactured by ADEKA) as a surfactant.
- each non-aqueous secondary battery electrode binder composition was applied onto a 20 ⁇ m thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a positive electrode having a positive electrode mixture layer having a thickness of 50 ⁇ m was produced.
- the positive electrode binder composition and the positive electrode obtained using the resin fine particle aqueous dispersions obtained in Examples 1 to 21 and Comparative Examples 1, 3, and 5 were compared with Examples 22 to 42, respectively.
- a positive electrode binder composition and a positive electrode according to Examples 8 to 10 were obtained.
- each non-aqueous secondary battery electrode binder composition was applied onto a 20 ⁇ m thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a negative electrode having a negative electrode mixture layer having a thickness of 50 ⁇ m was produced.
- the negative electrode binder compositions and negative electrodes obtained using the resin fine particle aqueous dispersions obtained in Examples 1 to 21 and Comparative Examples 1, 3, and 5 were compared with Examples 22 to 42, respectively. Negative electrode binder compositions and negative electrodes according to Examples 8 to 10 were obtained.
- Epoxy resin (Product name Adeka Resin EM-1-60L, manufactured by ADEKA Corporation, epoxy equivalent 320, bisphenol A-epichlorohydrin type epoxy resin) 1,4-bis (hydroxymethyl) cyclohexane; (Wako Pure Chemical Industries, Ltd.) Oxazoline group-containing acrylic / styrene resin; (product name Epocros K-2020E, manufactured by Nippon Shokubai Co., Ltd., oxazoline equivalent 550) Amicure VDH; (Ajinomoto Fine Techno Co., Ltd.) Carbodilite V-02; Carbodiimide curing agent (Nisshinbo Co., Ltd., NCN equivalent 600) Polyamide resin; copolymerized polyamide resin (product name Gritex D1500A Suspension, manufactured by EMS Chemie Japan Co., Ltd.)
- the resin fine particle aqueous dispersion obtained in Comparative Example 5 is a trifunctional epoxy resin [product name Denacol EX321, manufactured by Nagase ChemteX Corporation] ]
- the copolymer solution obtained in Comparative Example 6 with 50 parts of trifunctional epoxy resin [Denacol EX321] and the copolymer solution obtained in Comparative Example 7 with diaminodiphenyl ether [DPE / ODA, 50 parts of Wakayama Seika Kogyo Co., Ltd.), and what is dissolved in toluene, the final solid content of the binder composition is 50% It was adjusted to and kneaded to a nonaqueous secondary battery electrode binder composition was prepared.
- each non-aqueous secondary battery electrode binder composition was applied onto a 20 ⁇ m thick aluminum foil serving as a current collector using a doctor blade, dried by heating under reduced pressure, and subjected to a rolling process using a roll press. Then, a positive electrode having a positive electrode mixture layer having a thickness of 50 ⁇ m was produced.
- the positive electrode binder composition and the positive electrode obtained using the resin fine particle aqueous dispersion obtained in Comparative Example 5 and the copolymer solution obtained in Comparative Examples 6 and 7, respectively, were used as Comparative Example 11.
- each non-aqueous secondary battery electrode binder composition was applied onto a 20 ⁇ m thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a negative electrode having a negative electrode mixture layer having a thickness of 50 ⁇ m was produced.
- the resin fine particle water dispersion obtained in Comparative Example 5 and the negative electrode binder composition and negative electrode obtained using the copolymer solutions obtained in Comparative Examples 6 and 7 were respectively compared with Comparative Example 11.
- the lithium ion secondary battery electrode (positive electrode and negative electrode) obtained by the above method was used to evaluate the binding property and the electrolytic solution resistance, and the lithium ion secondary battery electrode (positive electrode and negative electrode) evaluation cell was used. Battery characteristics were evaluated.
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Abstract
Description
官能基含有架橋型樹脂微粒子が、
(A)1分子中に1つのエチレン性不飽和基と、単官能または多官能エポキシ基とを有する単量体(a)、1分子中に1つのエチレン性不飽和基と、単官能または多官能アミド基とを有する単量体(b)、および1分子中に1つのエチレン性不飽和基と、単官能または多官能水酸基とを有する単量体(c)からなる群より選ばれる少なくとも1つの単量体0.1~20重量%、
(B)1分子中に1つのエチレン性不飽和基と、単官能または多官能アルコキシシリル基とを有する単量体(d)、および1分子中に2つ以上のエチレン性不飽和基を有する単量体(e)からなる群より選ばれる少なくとも1つの単量体0.1~5重量%、および、
(C)前記単量体(a)~(e)以外の、エチレン性不飽和基を有する単量体(k)75~99.8重量%
を含むエチレン性不飽和基を有する単量体を水中にて界面活性剤の存在下、ラジカル重合開始剤によって乳化重合してなる樹脂微粒子であることを特徴とする、非水系二次電池電極用バインダー組成物に関する。 The first invention of the present invention is a binder composition for a non-aqueous secondary battery electrode comprising functional group-containing crosslinked resin fine particles,
Functional group-containing crosslinked resin fine particles
(A) Monomer having one ethylenically unsaturated group and monofunctional or polyfunctional epoxy group in one molecule (a) One ethylenically unsaturated group in one molecule and monofunctional or polyfunctional At least one selected from the group consisting of a monomer (b) having a functional amide group and a monomer (c) having one ethylenically unsaturated group and a monofunctional or polyfunctional hydroxyl group in one molecule. 0.1-20% by weight of one monomer,
(B) a monomer (d) having one ethylenically unsaturated group and a monofunctional or polyfunctional alkoxysilyl group in one molecule, and two or more ethylenically unsaturated groups in one molecule 0.1 to 5% by weight of at least one monomer selected from the group consisting of monomers (e), and
(C) Monomers having an ethylenically unsaturated group other than the monomers (a) to (e) (k) 75 to 99.8% by weight
Non-aqueous secondary battery electrode, characterized in that it is a resin fine particle obtained by emulsion polymerization of a monomer having an ethylenically unsaturated group containing water with a radical polymerization initiator in the presence of a surfactant in water The present invention relates to a binder composition.
本発明の非水系二次電池電極用バインダーは、特定の官能基を有するエチレン性不飽和単量体を含む単量体を共重合して得られる官能基含有架橋型樹脂微粒子を含むことを特徴とする。官能基含有架橋型樹脂微粒子が、特定の官能基による架橋構造をとることにより耐電解液性を確保し、また、官能基含有架橋型樹脂微粒子が、特定の官能基を含有することにより、集電体、または電極との密着性に寄与することができる。さらには架橋構造や官能基の量を調整することで、可とう性に優れた非水系二次電池電極用バインダー組成物を得ることができる。 <Functional Group-Containing Crosslinked Resin Fine Particles According to the Present Invention>
The binder for a non-aqueous secondary battery electrode of the present invention comprises functional group-containing crosslinked resin fine particles obtained by copolymerizing a monomer containing an ethylenically unsaturated monomer having a specific functional group. And The functional group-containing cross-linked resin fine particles have a cross-linked structure with a specific functional group to ensure the resistance to an electrolytic solution, and the functional group-containing cross-linked resin fine particles contain a specific functional group. This can contribute to the adhesion with the electric body or the electrode. Furthermore, the binder composition for non-aqueous secondary battery electrodes excellent in flexibility can be obtained by adjusting the amount of the crosslinked structure and functional group.
(A)1分子中に1つのエチレン性不飽和基と、単官能または多官能エポキシ基とを有する単量体(a)、1分子中に1つのエチレン性不飽和基と、単官能または多官能アミド基とを有する単量体(b)、および1分子中に1つのエチレン性不飽和基と、単官能または多官能水酸基とを有する単量体(c)からなる群より選ばれる少なくとも1つの単量体を0.1~20重量%
(B)1分子中に1つのエチレン性不飽和基と、アルコキシシリル基とを有する単量体(d)、および1分子中に2つ以上のエチレン性不飽和基を有する単量体(e)からなる群より選ばれる少なくとも1つの単量体を0.1~5重量%
(C)前記単量体(a)~(e)以外の、エチレン性不飽和基を有する単量体(k)を75~99.8重量% The functional group-containing crosslinked resin fine particles used in the binder composition for a non-aqueous secondary battery electrode of the present invention are obtained by emulsion polymerization of an ethylenically unsaturated monomer in water in the presence of a surfactant with a radical polymerization initiator. Resin fine particles obtained in this way. The functional group-containing crosslinked resin fine particles used in the present invention are obtained by emulsion polymerization of ethylenically unsaturated monomers containing the following monomer groups (A), (B) and (C) in the following proportions. Features.
(A) Monomer having one ethylenically unsaturated group and monofunctional or polyfunctional epoxy group in one molecule (a) One ethylenically unsaturated group in one molecule and monofunctional or polyfunctional At least one selected from the group consisting of a monomer (b) having a functional amide group and a monomer (c) having one ethylenically unsaturated group and a monofunctional or polyfunctional hydroxyl group in one molecule. 0.1-20% by weight of one monomer
(B) a monomer (d) having one ethylenically unsaturated group and an alkoxysilyl group in one molecule, and a monomer (e) having two or more ethylenically unsaturated groups in one molecule (e) 0.1 to 5% by weight of at least one monomer selected from the group consisting of
(C) 75 to 99.8% by weight of the monomer (k) having an ethylenically unsaturated group other than the monomers (a) to (e)
単量体群(A)に含まれる単量体を使用することにより、エポキシ基、アミド基、または水酸基を官能基含有架橋型樹脂微粒子の粒子内や表面に残存させることができ、これにより集電体の密着性などの物性を向上させることができる。単量体群(A)に含まれる単量体は、粒子合成後でもその官能基が粒子内部や表面に残存しやすく、少量でも集電体への密着性効果が大きい。また、その一部が架橋反応に使用されてもよく、これらの官能基の架橋度合いを調整することで、耐電解液性と密着性のバランスをとることができる。 <About monomer group (A)>
By using a monomer contained in the monomer group (A), an epoxy group, an amide group, or a hydroxyl group can be left in or on the surface of the functional group-containing crosslinked resin fine particles. It is possible to improve physical properties such as the adhesion of the electric body. The monomers contained in the monomer group (A) tend to remain in the inside and on the surface of the particles even after the synthesis of the particles, and a small amount of adhesion to the current collector is large. Moreover, a part of them may be used for the crosslinking reaction, and by adjusting the degree of crosslinking of these functional groups, it is possible to balance the resistance to electrolytic solution and the adhesion.
単量体群(B)に含まれる単量体の有する官能基(アルコキシシリル基、エチレン性不飽和基)は、自己架橋型反応性官能基であり、主に粒子合成中における粒子内部架橋を形成する効果がある。粒子の内部架橋を十分に行うことで、耐電解液性を向上させることができる。したがって、単量体群(B)に含まれる単量体を使用することで架橋型樹脂微粒子とすることができる。また、粒子架橋を十分に行うことで、耐電解液性を向上させることができる。 <About monomer group (B)>
The functional group (alkoxysilyl group, ethylenically unsaturated group) of the monomer contained in the monomer group (B) is a self-crosslinking reactive functional group, and is mainly used for particle internal cross-linking during particle synthesis. Has the effect of forming. Electrolytic solution resistance can be improved by sufficiently carrying out internal crosslinking of the particles. Therefore, it is possible to obtain crosslinked resin fine particles by using a monomer contained in the monomer group (B). In addition, by sufficiently carrying out particle crosslinking, the resistance to electrolytic solution can be improved.
本発明の非水系二次電池電極用バインダー組成物に用いる官能基含有架橋型樹脂微粒子は、上述した1分子中に1つのエチレン性不飽和基と、単官能または多官能の各種官能基を有する単量体(a)~(e)に加えて、単量体群(C)として、単量体(a)~(e)以外の、エチレン性不飽和基を有する単量体(k)を同時に乳化重合することで得ることができる。 <About monomer group (C)>
The functional group-containing crosslinked resin fine particles used in the binder composition for a non-aqueous secondary battery electrode according to the present invention have one ethylenically unsaturated group and various monofunctional or polyfunctional functional groups in one molecule. In addition to the monomers (a) to (e), the monomer group (C) includes monomers (k) having an ethylenically unsaturated group other than the monomers (a) to (e). It can be obtained by emulsion polymerization at the same time.
本発明の官能基含有架橋型樹脂微粒子は、従来既知の乳化重合方法により合成される。 <Method for producing functional group-containing crosslinked resin fine particles>
The functional group-containing crosslinked resin fine particles of the present invention are synthesized by a conventionally known emulsion polymerization method.
本発明において乳化重合の際に用いられる乳化剤としては、エチレン性不飽和基を有する反応性乳化剤やエチレン性不飽和基を有しない非反応性乳化剤など、従来公知のものを任意に使用することができる。 <Emulsifier used in emulsion polymerization>
As the emulsifier used in the emulsion polymerization in the present invention, a conventionally known one such as a reactive emulsifier having an ethylenically unsaturated group or a non-reactive emulsifier having no ethylenically unsaturated group may be arbitrarily used. it can.
本発明の官能基含有架橋型樹脂微粒子の乳化重合に際して用いられる水性媒体としては、水があげられ、親水性の有機溶剤も本発明の目的を損なわない範囲で使用することができる。 <Aqueous medium used in emulsion polymerization>
The aqueous medium used in the emulsion polymerization of the functional group-containing crosslinked resin fine particles of the present invention includes water, and a hydrophilic organic solvent can be used as long as the object of the present invention is not impaired.
本発明の官能基含有架橋型樹脂微粒子を得るに際して用いられる重合開始剤としては、ラジカル重合を開始する能力を有するものであれば特に制限はなく、公知の油溶性重合開始剤や水溶性重合開始剤を使用することができる。 <Polymerization initiator used in emulsion polymerization>
The polymerization initiator used in obtaining the functional group-containing cross-linked resin fine particles of the present invention is not particularly limited as long as it has the ability to initiate radical polymerization, and is a known oil-soluble polymerization initiator or water-soluble polymerization start. Agents can be used.
なお、前記した重合開始剤によらずとも、光化学反応や、放射線照射などによっても重合を行うことができる。重合温度は各重合開始剤の重合開始温度以上とする。例えば、過酸化物系重合開始剤では、通常70℃程度とすればよい。重合時間は特に制限されないが、通常2~24時間である。 <Conditions for emulsion polymerization>
In addition, it can superpose | polymerize by a photochemical reaction, radiation irradiation, etc. irrespective of an above described polymerization initiator. The polymerization temperature is not less than the polymerization start temperature of each polymerization initiator. For example, in the case of a peroxide-based polymerization initiator, it may be usually about 70 ° C. The polymerization time is not particularly limited, but is usually 2 to 24 hours.
さらに必要に応じて、緩衝剤として、酢酸ナトリウム、クエン酸ナトリウム、重炭酸ナトリウムなどが、また、連鎖移動剤としてのオクチルメルカプタン、チオグリコール酸2-エチルヘキシル、チオグリコール酸オクチル、ステアリルメルカプタン、ラウリルメルカプタン、t-ドデシルメルカプタンなどのメルカプタン類が適量使用できる。 <Other materials used for reaction>
Further, if necessary, sodium acetate, sodium citrate, sodium bicarbonate and the like as a buffering agent, and octyl mercaptan, 2-ethylhexyl thioglycolate, octyl thioglycolate, stearyl mercaptan, lauryl mercaptan as a chain transfer agent A suitable amount of mercaptans such as t-dodecyl mercaptan can be used.
<ガラス転移温度>
また、官能基含有架橋型樹脂微粒子のガラス転移温度(以下、Tgともいう)は、-30~70℃が好ましく、-20~30℃がさらに好ましい。Tgが-30℃未満の場合、バインダーが過度に電極活物質を覆い、インピーダンスが高くなりやすい。また、Tg が70℃を超えると、バインダーの柔軟性、粘着性が乏しくなり、電極活物質の集電材への接着性、電極の成形性が劣る場合がある。なお、ガラス転移温度は、DSC(示差走査熱量計)を用いて求めた値である。 <Characteristics of functional group-containing crosslinked resin fine particles>
<Glass transition temperature>
The glass transition temperature (hereinafter also referred to as Tg) of the functional group-containing crosslinked resin fine particles is preferably −30 to 70 ° C., more preferably −20 to 30 ° C. When Tg is less than −30 ° C., the binder excessively covers the electrode active material, and the impedance tends to increase. On the other hand, when Tg exceeds 70 ° C., the flexibility and tackiness of the binder become poor, and the adhesion of the electrode active material to the current collector and the moldability of the electrode may be inferior. The glass transition temperature is a value obtained using a DSC (differential scanning calorimeter).
また、本発明においては官能基含有架橋型樹脂微粒子の粒子構造を多層構造、いわゆるコアシェル粒子にすることもできる。例えば、コア部、またはシェル部に官能基を有する単量体を主に重合させた樹脂を局在化させたり、コアとシェルによってTgや組成に差を設けたりすることにより、硬化性、乾燥性、成膜性、バインダーの機械強度を向上させることができる。 <Particle structure>
In the present invention, the particle structure of the functional group-containing crosslinked resin fine particles may be a multi-layer structure, so-called core-shell particles. For example, it is possible to localize a resin in which a monomer having a functional group is mainly polymerized in the core part or the shell part, or to provide a difference in Tg or composition between the core and the shell, thereby improving the curability and drying. Property, film formability, and mechanical strength of the binder can be improved.
官能基含有架橋型樹脂微粒子の平均粒子径は、電極活物質の結着性や粒子の安定性の点から、10~500nmであることが好ましく、30~250nmであることがより好ましい。また、1μmを超えるような粗大粒子が多く含有されるようになると粒子の安定性が損なわれるので、1μmを超える粗大粒子は多くとも5重量%以下であることが好ましい。なお、本発明における平均粒子径とは、体積平均粒子径のことを表し、動的光散乱法により測定できる。 <Particle size>
The average particle size of the functional group-containing crosslinked resin fine particles is preferably 10 to 500 nm, more preferably 30 to 250 nm, from the viewpoint of the binding property of the electrode active material and the stability of the particles. Further, when a large amount of coarse particles exceeding 1 μm are contained, the stability of the particles is impaired, so that the coarse particles exceeding 1 μm are preferably at most 5% by weight. In addition, the average particle diameter in the present invention represents a volume average particle diameter and can be measured by a dynamic light scattering method.
さらに官能基含有架橋型樹脂微粒子を成膜して得られる塗膜の強度、および伸び率は、樹脂の強靭性の点から、強度1.0~7.0N/mm2、伸び率300~2000%であることが好ましく、さらには強度2.0~5.5N/mm2、伸び率400~1200%であることがより好ましい。強度が1.0N/mm2未満であると活物質の保持力や集電体への結着力が悪くなる場合があり、また、強度が7.0N/mm2を超えると塗膜が剛直になりすぎて結着力が悪くなる。伸び率が300%未満であると、塗膜がもろく、結着力が十分得られない場合がある。また、伸び率が2000%を超えると、活物質の保持力や集電体への結着力が悪くなる場合がある。なお、本発明における塗膜の強度、および伸び率とは、テンシロンにより測定した破断強度、破断伸度のことである。 <Strength of coating film, elongation>
Furthermore, the strength and elongation of the coating film obtained by forming the functional group-containing crosslinked resin fine particles are 1.0 to 7.0 N / mm 2 in strength and 300 to 2000 in terms of the toughness of the resin. %, More preferably a strength of 2.0 to 5.5 N / mm 2 and an elongation of 400 to 1200%. Strength might binding force to the holding force and the current collector of the active material is less than 1.0 N / mm 2 is deteriorated, and strength coating film rigidly exceeds 7.0 N / mm 2 It becomes too much and the binding power becomes worse. When the elongation is less than 300%, the coating film is fragile and sufficient binding strength may not be obtained. Moreover, when elongation rate exceeds 2000%, the retention strength of an active material and the binding force to a collector may worsen. In addition, the intensity | strength and elongation rate of the coating film in this invention are the breaking strength and breaking elongation measured with Tensilon.
さらに本発明の官能基含有架橋型樹脂微粒子を成膜して得られる塗膜のゲル分率は、50%以上、さらには70%以上であることが好ましい。ゲル分率とは、樹脂微粒子を成膜して得られる塗膜を有機溶剤(ここで有機溶剤とは、メタノール、エタノール、酢酸エチル、メチルエチルケトン、トルエン、シクロヘキサンなどの汎用的に使用される溶媒、またはプロピレンカーボネート、エチルカーボネートなどの二次電池電解液として使用される溶媒などのことを言う)に一定時間浸漬後、有機溶剤に溶解せずに形状を保持している樹脂分のことをいう。 <Gel fraction>
Furthermore, the gel fraction of the coating film obtained by forming the functional group-containing crosslinked resin fine particles of the present invention is preferably 50% or more, and more preferably 70% or more. Gel fraction refers to a coating obtained by forming resin fine particles into an organic solvent (wherein organic solvent is a commonly used solvent such as methanol, ethanol, ethyl acetate, methyl ethyl ketone, toluene, cyclohexane, Or a solvent used as a secondary battery electrolyte such as propylene carbonate or ethyl carbonate), which is a resin component that retains its shape without being dissolved in an organic solvent after being immersed for a certain period of time.
本発明の非水系二次電池電極用バインダー組成物は、官能基含有架橋型樹脂微粒子に加えて、さらに、未架橋のエポキシ基含有化合物、未架橋のアミド基含有化合物、未架橋の水酸基含有化合物、および未架橋のオキサゾリン基含有化合物からなる群より選ばれる少なくとも1つの未架橋の化合物(D)[以下、化合物(D)と表記する場合がある]とを含むことが好ましい。 <Uncrosslinked compound (D) added to polymerized fine resin particles>
The binder composition for a non-aqueous secondary battery electrode of the present invention includes, in addition to the functional group-containing crosslinked resin fine particles, an uncrosslinked epoxy group-containing compound, an uncrosslinked amide group-containing compound, and an uncrosslinked hydroxyl group-containing compound. And at least one uncrosslinked compound (D) selected from the group consisting of uncrosslinked oxazoline group-containing compounds [hereinafter sometimes referred to as compound (D)].
未架橋のエポキシ基含有化合物としては、例えば、グリシジル(メタ)アクリレート、3,4-エポキシシクロヘキシル(メタ)アクリレートなどのエポキシ基含有エチレン性不飽和単量体;前記エポキシ基含有エチレン性不飽和単量体を含むエチレン性不飽和単量体を重合して得られるラジカル重合系樹脂;エチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、グリセリンジグリシジルエーテル、グリセリントリグリシジルエーテル、1,6-ヘキサンジオールジグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ジグリシジルアニリン、N,N,N’,N’-テトラグリシジル-m-キシリレンジアミン、1,3-ビス(N,N’-ジグリシジルアミノメチル)シクロヘキサンなどの多官能エポキシ化合物;ビスフェノールA-エピクロロヒドリン型エポキシ樹脂、ビスフェノールF-エピクロロヒドリン型エポキシ樹脂などのエポキシ系樹脂などがあげられる。 <Uncrosslinked epoxy group-containing compound>
Examples of the uncrosslinked epoxy group-containing compound include epoxy group-containing ethylenically unsaturated monomers such as glycidyl (meth) acrylate and 3,4-epoxycyclohexyl (meth) acrylate; Radical polymerization resins obtained by polymerizing ethylenically unsaturated monomers containing monomers; ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, glycerin triglycidyl ether, 1,6-hexanediol Diglycidyl ether, trimethylolpropane triglycidyl ether, diglycidyl aniline, N, N, N ′, N′-tetraglycidyl-m-xylylenediamine, 1,3-bis (N, N′-diglycidylaminomethyl) Cyclohexane Polyfunctional epoxy compounds; bisphenol A- epichlorohydrin epoxy resins, and epoxy resins such as bisphenol F- epichlorohydrin type epoxy resin.
未架橋のアミド基含有化合物としては、例えば、(メタ)アクリルアミドなどの第一アミド基含有化合物;N-メチロールアクリルアミド、N,N-ジ(メチロール)アクリルアミド、N-メチロール-N-メトキシメチル(メタ)アクリルアミドなどのアルキロール(メタ)アクリルアミド系化合物;N-メトキシメチル-(メタ)アクリルアミド、N-エトキシメチル-(メタ)アクリルアミド、N-プロポキシメチル-(メタ)アクリルアミド、N-ブトキシメチル-(メタ)アクリルアミド、N-ペントキシメチル-(メタ)アクリルアミドなどのモノアルコキシ(メタ)アクリルアミド系化合物;N,N-ジ(メトキシメチル)アクリルアミド、N-エトキシメチル-N-メトキシメチルメタアクリルアミド、N,N-ジ(エトキシメチル)アクリルアミド、N-エトキシメチル-N-プロポキシメチルメタアクリルアミド、N,N-ジ(プロポキシメチル)アクリルアミド、N-ブトキシメチル-N-(プロポキシメチル)メタアクリルアミド、N,N-ジ(ブトキシメチル)アクリルアミド、N-ブトキシメチル-N-(メトキシメチル)メタアクリルアミド、N,N-ジ(ペントキシメチル)アクリルアミド、N-メトキシメチル-N-(ペントキシメチル)メタアクリルアミドなどのジアルコキシ(メタ)アクリルアミド系化合物;N,N-ジメチルアミノプロピルアクリルアミド、N,N-ジエチルアミノプロピルアクリルアミドなどのジアルキルアミノ(メタ)アクリルアミド系化合物;N,N-ジメチルアクリルアミド、N,N-ジエチルアクリルアミドなどのジアルキル(メタ)アクリルアミド系化合物;ダイアセトン(メタ)アクリルアミドなどのケト基含有(メタ)アクリルアミド系化合物など、以上のアミド基含有エチレン性不飽和単量体;前記アミド基含有エチレン性不飽和単量体を含むエチレン性不飽和単量体を重合して得られるラジカル重合系樹脂などがあげられる。 <Uncrosslinked amide group-containing compound>
Non-crosslinked amide group-containing compounds include, for example, primary amide group-containing compounds such as (meth) acrylamide; N-methylolacrylamide, N, N-di (methylol) acrylamide, N-methylol-N-methoxymethyl (meta) ) Alkyrol (meth) acrylamide compounds such as acrylamide; N-methoxymethyl- (meth) acrylamide, N-ethoxymethyl- (meth) acrylamide, N-propoxymethyl- (meth) acrylamide, N-butoxymethyl- (meta ) Monoalkoxy (meth) acrylamide compounds such as acrylamide and N-pentoxymethyl- (meth) acrylamide; N, N-di (methoxymethyl) acrylamide, N-ethoxymethyl-N-methoxymethylmethacrylamide, N, N -Di (Etoki Methyl) acrylamide, N-ethoxymethyl-N-propoxymethylmethacrylamide, N, N-di (propoxymethyl) acrylamide, N-butoxymethyl-N- (propoxymethyl) methacrylamide, N, N-di (butoxymethyl) Dialkoxy (meth) acrylamides such as acrylamide, N-butoxymethyl-N- (methoxymethyl) methacrylamide, N, N-di (pentoxymethyl) acrylamide, N-methoxymethyl-N- (pentoxymethyl) methacrylamide Compounds; dialkylamino (meth) acrylamide compounds such as N, N-dimethylaminopropylacrylamide and N, N-diethylaminopropylacrylamide; N, N-dimethylacrylamide and N, N-diethylacrylamide Any dialkyl (meth) acrylamide compound; keto group-containing (meth) acrylamide compound such as diacetone (meth) acrylamide or the like, and the above amide group-containing ethylenically unsaturated monomers; Examples thereof include a radical polymerization resin obtained by polymerizing an ethylenically unsaturated monomer containing a monomer.
未架橋の水酸基含有化合物としては、例えば、2-ヒドロキシエチル(メタ)アクリレート、2-ヒドロキシプロピル(メタ)アクリレート、4-ヒドロキシブチル(メタ)アクリレート、グリセロールモノ(メタ)アクリレート4-ヒドロキシビニルベンゼン、1-エチニル-1-シクロヘキサノール、アリルアルコールなどの水酸基含有エチレン性不飽和単量体;前記水酸基含有エチレン性不飽和単量体を含むエチレン性不飽和単量体を重合して得られるラジカル重合系樹脂;エチレングリコール、ジエチレングリコール、1,3-プロパンジオール、1,4-ブタンジオール、1,5-ペンタンジオール、1,6-ヘキサンジオールなどの直鎖脂肪族ジオール類;プロピレングリコール、ネオペンチルグリコール、3-メチル-1,5-ペンタンジオール、2,2-ジエチル-1,3-プロパンジオールなどの分岐鎖脂肪族ジオール類;1,4-ビス(ヒドロキシメチル)シクロヘキサンなどの環状ジオール類などがあげられる。 <Uncrosslinked hydroxyl group-containing compound>
Examples of the uncrosslinked hydroxyl group-containing compound include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, glycerol mono (meth) acrylate 4-hydroxyvinylbenzene, Hydroxyl group-containing ethylenically unsaturated monomers such as 1-ethynyl-1-cyclohexanol and allyl alcohol; radical polymerization obtained by polymerizing ethylenically unsaturated monomers containing the hydroxyl group-containing ethylenically unsaturated monomers Resins: linear aliphatic diols such as ethylene glycol, diethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol; propylene glycol, neopentyl glycol , 3-methyl-1,5 Pentanediol, 2,2-branched aliphatic diols such as diethyl-1,3-propanediol; and 1,4-bis cyclic diol such as (hydroxymethyl) cyclohexane.
未架橋のオキサゾリン基含有化合物としては、例えば、2’-メチレンビス(2-オキサゾリン)、2,2’-エチレンビス(2-オキサゾリン)、2,2’-エチレンビス(4-メチル-2-オキサゾリン)、2,2’-プロピレンビス(2-オキサゾリン)、2,2’-テトラメチレンビス(2-オキサゾリン)、2,2’-ヘキサメチレンビス(2-オキサゾリン)、2,2’-オクタメチレンビス(2-オキサゾリン)、2,2’-p-フェニレンビス(2-オキサゾリン)、2,2’-p-フェニレンビス(4,4’-ジメチル-2-オキサゾリン)、2,2’-p-フェニレンビス(4-メチル-2-オキサゾリン)、2,2’-p-フェニレンビス(4-フェニル-2-オキサゾリン)、2,2’-m-フェニレンビス(2-オキサゾリン)、2,2’-m-フェニレンビス(4-メチル-2-オキサゾリン)、2,2’-m-フェニレンビス(4,4’-ジメチル-2-オキサゾリン)、2,2’-m-フェニレンビス(4-フェニレンビス-2-オキサゾリン)、2,2’-o-フェニレンビス(2-オキサゾリン)、2,2’-o-フェニレンビス(4-メチル-2-オキサゾリン)、2,2’-ビス(2-オキサゾリン)、2,2’-ビス(4-メチル-2-オキサゾリン)、2,2’-ビス(4-エチル-2-オキサゾリン)、2,2’-ビス(4-フェニル-2-オキサゾリン)、さらにはオキサゾリン基含有ラジカル重合系樹脂などがあげられる。 <Uncrosslinked oxazoline group-containing compound>
Examples of the uncrosslinked oxazoline group-containing compound include 2′-methylenebis (2-oxazoline), 2,2′-ethylenebis (2-oxazoline), and 2,2′-ethylenebis (4-methyl-2-oxazoline). ), 2,2′-propylenebis (2-oxazoline), 2,2′-tetramethylenebis (2-oxazoline), 2,2′-hexamethylenebis (2-oxazoline), 2,2′-octamethylene Bis (2-oxazoline), 2,2'-p-phenylenebis (2-oxazoline), 2,2'-p-phenylenebis (4,4'-dimethyl-2-oxazoline), 2,2'-p -Phenylenebis (4-methyl-2-oxazoline), 2,2'-p-phenylenebis (4-phenyl-2-oxazoline), 2,2'-m-phenylenebis (2-oxazoline), 2 , 2'-m-phenylenebis (4-methyl-2-oxazoline), 2,2'-m-phenylenebis (4,4'-dimethyl-2-oxazoline), 2,2'-m-phenylenebis ( 4-phenylenebis-2-oxazoline), 2,2′-o-phenylenebis (2-oxazoline), 2,2′-o-phenylenebis (4-methyl-2-oxazoline), 2,2′-bis (2-oxazoline), 2,2′-bis (4-methyl-2-oxazoline), 2,2′-bis (4-ethyl-2-oxazoline), 2,2′-bis (4-phenyl-2) -Oxazoline), and oxazoline group-containing radical polymerization resins.
化合物(D)は、官能基含有架橋型樹脂微粒子の固形分100重量部に対して0.1~50重量部添加するのが好ましく、5~40重量部添加するのがさらに好ましい。化合物(D)の添加量が0.1重量部未満であると、集電体の密着性に寄与する官能基の量が少なくなり、集電体の密着性向上に十分寄与できない場合がある。また、50重量部を超えると、化合物(D)の電解液への漏出など、バインダー性能への悪影響を起こす場合がある。さらに、化合物(D)は2種類以上併用することも可能である。 <Addition amount of compound (D), molecular weight>
Compound (D) is preferably added in an amount of 0.1 to 50 parts by weight, more preferably 5 to 40 parts by weight, based on 100 parts by weight of the solid content of the functional group-containing crosslinked resin fine particles. When the addition amount of the compound (D) is less than 0.1 parts by weight, the amount of the functional group contributing to the adhesion of the current collector is decreased, and may not sufficiently contribute to the improvement of the adhesion of the current collector. On the other hand, when the amount exceeds 50 parts by weight, adverse effects on the binder performance such as leakage of the compound (D) into the electrolyte solution may occur. Furthermore, two or more types of compounds (D) can be used in combination.
本発明の非水系二次電池電極用バインダー組成物には、官能基含有架橋型樹脂微粒子および化合物(D)以外に、バインダーの可とう性や耐電解液性を調整する目的で第3成分を添加することもできる。 <Third component in the composition of the present invention>
In addition to the functional group-containing crosslinked resin fine particles and the compound (D), the binder composition for a non-aqueous secondary battery electrode according to the present invention contains a third component for the purpose of adjusting the flexibility and electrolyte resistance of the binder. It can also be added.
第3成分としては、例えば官能基含有架橋型樹脂微粒子と化合物(D)、または化合物(D)同士を架橋させる架橋剤(化合物(l))を添加することができる。 <Crosslinking agent>
As the third component, for example, a functional group-containing cross-linked resin fine particle and the compound (D), or a cross-linking agent (compound (l)) that cross-links the compounds (D) can be added.
本発明の官能基含有架橋型樹脂微粒子を含む非水系二次電池電極用バインダー組成物には、成膜助剤、消泡剤、レベリング剤、防腐剤、pH調整剤、粘性調整剤などを必要に応じて配合できる。 <Third component such as film forming aid>
The binder composition for non-aqueous secondary battery electrodes containing the functional group-containing crosslinked resin fine particles of the present invention requires a film forming aid, an antifoaming agent, a leveling agent, a preservative, a pH adjusting agent, a viscosity adjusting agent, and the like. It can be blended according to.
本発明の非水系二次電池電極用バインダー組成物は、二次電池の正極、および負極に使用することができる。その他、エネルギーデバイス、すなわち、キャパシタ、リチウムイオンキャパシタ、太陽電池などにも使用することができる。 <Use Mode of Binder Composition of the Present Invention>
The binder composition for nonaqueous secondary battery electrodes of the present invention can be used for a positive electrode and a negative electrode of a secondary battery. In addition, it can be used for energy devices, that is, capacitors, lithium ion capacitors, solar cells, and the like.
[実施例1]
攪拌器、温度計、滴下ロート、還流器を備えた反応容器に、イオン交換水40部と界面活性剤としてアデカリアソープSR-10(株式会社ADEKA製)0.2部とを仕込み、別途、スチレン50部、2-エチルヘキシルアクリレート45部、メチルメタクリレート1.5部、アクリル酸1部、ダイアセトンアクリルアミド2部、3-メタクリロキシプロピルトリメトキシシラン0.5部、イオン交換水53部および界面活性剤としてアデカリアソープSR-10(株式会社ADEKA製)1.8部をあらかじめ混合しておいたプレエマルジョンのうちの1%をさらに加えた。内温を70℃に昇温し十分に窒素置換した後、過硫酸カリウムの5%水溶液10部の10%を添加し重合を開始した。反応系内を70℃で5分間保持した後、内温を70℃に保ちながらプレエマルジョンの残りと過硫酸カリウムの5%水溶液の残りを3時間かけて滴下し、さらに2時間攪拌を継続した。固形分測定にて転化率が98%超えたことを確認後、温度を30℃まで冷却した。25%アンモニア水を添加して、pHを8.5とし、さらにイオン交換水で固形分を48%に調整して樹脂微粒子水分散体を得た。なお、固形分は、150℃20分焼き付け残分により求めた。 <Preparation of aqueous dispersion of resin fine particles>
[Example 1]
A reaction vessel equipped with a stirrer, a thermometer, a dropping funnel, and a refluxing vessel was charged with 40 parts of ion-exchanged water and 0.2 part of Adeka Soap SR-10 (manufactured by ADEKA) as a surfactant. 50 parts of styrene, 45 parts of 2-ethylhexyl acrylate, 1.5 parts of methyl methacrylate, 1 part of acrylic acid, 2 parts of diacetone acrylamide, 0.5 part of 3-methacryloxypropyltrimethoxysilane, 53 parts of ion-exchanged water and surface activity As an agent, 1% of a pre-emulsion in which 1.8 parts of Adekari Soap SR-10 (manufactured by ADEKA Corporation) was mixed in advance was further added. After raising the internal temperature to 70 ° C. and sufficiently substituting with nitrogen, 10% of 10 parts of a 5% aqueous solution of potassium persulfate was added to initiate polymerization. After maintaining the reaction system at 70 ° C. for 5 minutes, the remaining pre-emulsion and the remaining 5% aqueous solution of potassium persulfate were added dropwise over 3 hours while maintaining the internal temperature at 70 ° C., and stirring was further continued for 2 hours. . After confirming that the conversion rate exceeded 98% by solid content measurement, the temperature was cooled to 30 ° C. 25% aqueous ammonia was added to adjust the pH to 8.5, and the solid content was adjusted to 48% with ion-exchanged water to obtain a resin fine particle water dispersion. In addition, solid content was calculated | required by 150 degreeC 20 minute baking residue.
表1、表2に示す配合組成で、実施例1と同様の方法で合成し、実施例2~21、および、比較例1~5の樹脂微粒子水分散体を得た。ただし、比較例2、4は乳化重合時に樹脂が凝集し、目的の樹脂微粒子を得ることができなかった。 [Examples 2 to 21 and Comparative Examples 1 to 5]
The compounding compositions shown in Tables 1 and 2 were synthesized in the same manner as in Example 1 to obtain resin fine particle aqueous dispersions of Examples 2 to 21 and Comparative Examples 1 to 5. However, in Comparative Examples 2 and 4, the resin aggregated during emulsion polymerization, and the desired resin fine particles could not be obtained.
アデカリアソープSR-10;アルキルエーテル系アニオン界面活性剤(株式会社ADEKA製)
アデカリアソープER-20;アルキルエーテル系ノニオン界面活性剤(株式会社ADEKA製) The explanation of the product names in Tables 1 and 2 is as follows.
ADEKA rear soap SR-10; alkyl ether anionic surfactant (manufactured by ADEKA Corporation)
ADEKA rear soap ER-20; alkyl ether nonionic surfactant (manufactured by ADEKA Corporation)
[比較例6]
攪拌器、温度計、滴下ロート、還流器を備えた反応容器に、イソプロピルアルコール40部を仕込み、別途、ブチルアクリレート80部、アクリル酸20部を滴下槽1に、また、アゾビスイソブチロニトリル2部をイソプロピルアルコール60部に溶解させて滴下槽2に仕込んだ。内温を70℃に昇温し十分に窒素置換した後、滴下槽1、2を2時間かけて滴下し、重合を行った。滴下終了後、内温を70℃に保ったまま1時間攪拌を続け、固形分測定にて転化率が98%超えたことを確認後、温度を30℃まで冷却し、固形分50%のブチルアクリレート/アクリル酸共重合体溶液を得た。なお、固形分は、150℃20分焼き付け残分により求めた。 <Preparation of butyl acrylate / acrylic acid copolymer solution>
[Comparative Example 6]
Into a reaction vessel equipped with a stirrer, thermometer, dropping funnel, and reflux condenser, 40 parts of isopropyl alcohol was charged, and 80 parts of butyl acrylate and 20 parts of acrylic acid were separately added to the dropping tank 1, and azobisisobutyronitrile. 2 parts were dissolved in 60 parts of isopropyl alcohol and charged into the dropping tank 2. After the internal temperature was raised to 70 ° C. and sufficiently substituted with nitrogen, the dropping tanks 1 and 2 were dropped over 2 hours to carry out polymerization. After completion of dropping, stirring was continued for 1 hour while maintaining the internal temperature at 70 ° C. After confirming that the conversion rate exceeded 98% by solid content measurement, the temperature was cooled to 30 ° C. and butyl having a solid content of 50%. An acrylate / acrylic acid copolymer solution was obtained. In addition, solid content was calculated | required by 150 degreeC 20 minute baking residue.
[比較例7]
比較例6と同様の方法でメチルメタクリレート88部とグリシジルメタクリレート12部とを使用して固形分50%のメチルメタクリレート/グリシジルメタクリレート共重合体溶液を得た。 <Preparation of methyl methacrylate / glycidyl methacrylate copolymer solution>
[Comparative Example 7]
A methyl methacrylate / glycidyl methacrylate copolymer solution having a solid content of 50% was obtained using 88 parts of methyl methacrylate and 12 parts of glycidyl methacrylate in the same manner as in Comparative Example 6.
[製造例1]
攪拌器、温度計、滴下ロート、還流器を備えた反応容器にイソプロピルアルコール20部、水20部を仕込み、別途、メチルメタクリレート40部、メチルアクリレート40部、グリシジルメタクリレート20部を滴下槽1に、また、過硫酸カリウム2部をイソプロピルアルコール30部および水30部に溶解させて滴下槽2に仕込んだ。内温を80℃に昇温し十分に窒素置換した後、滴下槽1、2を2時間かけて滴下し、重合を行った。滴下終了後、内温を80℃に保ったまま1時間攪拌を続け、固形分測定にて転化率が98%超えたことを確認後、温度を30℃まで冷却し、固形分50%のエポキシ基含有化合物(メチルメタクリレート/メチルアクリレート/グリシジルメタクリレート共重合体)溶液を得た。なお、固形分は、150℃20分焼き付け残分により求めた。 <Production of Compound (D) [Production of Epoxy Group-Containing Compound]>
[Production Example 1]
Into a reaction vessel equipped with a stirrer, thermometer, dropping funnel and refluxing vessel, 20 parts of isopropyl alcohol and 20 parts of water were charged, and 40 parts of methyl methacrylate, 40 parts of methyl acrylate and 20 parts of glycidyl methacrylate were separately added to the dropping tank 1, Moreover, 2 parts of potassium persulfate was dissolved in 30 parts of isopropyl alcohol and 30 parts of water, and charged into the dropping tank 2. After the internal temperature was raised to 80 ° C. and sufficiently substituted with nitrogen, the dropping tanks 1 and 2 were dropped over 2 hours to carry out polymerization. After completion of the dropwise addition, stirring was continued for 1 hour while maintaining the internal temperature at 80 ° C. After confirming that the conversion rate exceeded 98% by solid content measurement, the temperature was cooled to 30 ° C., and an epoxy having a solid content of 50% A group-containing compound (methyl methacrylate / methyl acrylate / glycidyl methacrylate copolymer) solution was obtained. In addition, solid content was calculated | required by 150 degreeC 20 minute baking residue.
[製造例2]
攪拌器、温度計、滴下ロート、還流器を備えた反応容器に、水90部を仕込み、別途、アクリルアミド20部を滴下槽1に、また、過硫酸カリウム2部を水90部に溶解させて滴下槽2に仕込んだ。内温を80℃に昇温し十分に窒素置換した後、滴下槽1、2を2時間かけて滴下し、重合を行った。滴下終了後、内温を80℃に保ったまま1時間攪拌を続け、固形分測定にて転化率が98%超えたことを確認後、温度を30℃まで冷却し、固形分10%のアミド基含有化合物(ポリアクリルアミド)溶液を得た。なお、固形分は、150℃20分焼き付け残分により求めた。 <Production of Compound (D) [Production of Amide Group-Containing Compound]>
[Production Example 2]
A reaction vessel equipped with a stirrer, a thermometer, a dropping funnel and a refluxing vessel was charged with 90 parts of water. Separately, 20 parts of acrylamide was dissolved in the dropping tank 1 and 2 parts of potassium persulfate was dissolved in 90 parts of water. The dropping tank 2 was charged. After the internal temperature was raised to 80 ° C. and sufficiently substituted with nitrogen, the dropping tanks 1 and 2 were dropped over 2 hours to carry out polymerization. After completion of dropping, stirring was continued for 1 hour while maintaining the internal temperature at 80 ° C. After confirming that the conversion rate exceeded 98% by solid content measurement, the temperature was cooled to 30 ° C., and the amide having a solid content of 10% was obtained. A group-containing compound (polyacrylamide) solution was obtained. In addition, solid content was calculated | required by 150 degreeC 20 minute baking residue.
攪拌器、温度計、滴下ロート、還流器を備えた反応容器に、水40部を仕込み、別途、2-エチルヘキシルアクリレート40部、スチレン40部、ジメチルアクリルアミド20部を滴下槽1に、また、過硫酸カリウム2部を水60部に溶解させて滴下槽2に仕込んだ。内温を80℃に昇温し十分に窒素置換した後、滴下槽1、2を2時間かけて滴下し、重合を行った。滴下終了後、内温を80℃に保ったまま1時間攪拌を続け、固形分測定にて転化率が98%超えたことを確認後、温度を30℃まで冷却し、固形分50%のアミド基含有化合物(2-エチルヘキシルアクリレート/スチレン/ジメチルアクリルアミド共重合体)溶液を得た。なお、固形分は、150℃20分焼き付け残分により求めた。 [Production Example 3]
A reaction vessel equipped with a stirrer, a thermometer, a dropping funnel and a refluxing vessel was charged with 40 parts of water. Separately, 40 parts of 2-ethylhexyl acrylate, 40 parts of styrene and 20 parts of dimethylacrylamide were added to the dropping tank 1, and 2 parts of potassium sulfate was dissolved in 60 parts of water and charged into the dropping tank 2. After the internal temperature was raised to 80 ° C. and sufficiently substituted with nitrogen, the dropping tanks 1 and 2 were dropped over 2 hours to carry out polymerization. After completion of the dropping, stirring was continued for 1 hour while maintaining the internal temperature at 80 ° C. After confirming that the conversion rate exceeded 98% by solid content measurement, the temperature was cooled to 30 ° C., and the amide having a solid content of 50% was obtained. A group-containing compound (2-ethylhexyl acrylate / styrene / dimethylacrylamide copolymer) solution was obtained. In addition, solid content was calculated | required by 150 degreeC 20 minute baking residue.
[製造例4]
攪拌器、温度計、滴下ロート、還流器を備えた反応容器に、イソプロピルアルコール20部、水20部を仕込み、別途、メチルメタクリレート40部、ブチルアクリレート40部、2-ヒドロキシエチルメタクリレート20部を滴下槽1に、また、過硫酸カリウム2部をイソプロピルアルコール30部および水30部に溶解させて滴下槽2に仕込んだ。内温を80℃に昇温し十分に窒素置換した後、滴下槽1、2を2時間かけて滴下し、重合を行った。滴下終了後、内温を80℃に保ったまま1時間攪拌を続け、固形分測定にて転化率が98%超えたことを確認後、温度を30℃まで冷却し、固形分50%の水酸基含有化合物(メチルメタクリレート/ブチルアクリレート/2-ヒドロキシエチルメタクリレート共重合体)溶液を得た。なお、固形分は、150℃20分焼き付け残分により求めた。 <Production of Compound (D) [Production of Hydroxyl-Containing Compound]>
[Production Example 4]
Into a reaction vessel equipped with a stirrer, thermometer, dropping funnel, and reflux condenser, 20 parts of isopropyl alcohol and 20 parts of water are charged, and 40 parts of methyl methacrylate, 40 parts of butyl acrylate, and 20 parts of 2-hydroxyethyl methacrylate are separately added dropwise. In the tank 1, 2 parts of potassium persulfate was dissolved in 30 parts of isopropyl alcohol and 30 parts of water and charged into the dropping tank 2. After the internal temperature was raised to 80 ° C. and sufficiently substituted with nitrogen, the dropping tanks 1 and 2 were dropped over 2 hours to carry out polymerization. After completion of the dropping, stirring was continued for 1 hour while maintaining the internal temperature at 80 ° C. After confirming that the conversion rate exceeded 98% by solid content measurement, the temperature was cooled to 30 ° C., and a hydroxyl group having a solid content of 50%. A solution containing compound (methyl methacrylate / butyl acrylate / 2-hydroxyethyl methacrylate copolymer) was obtained. In addition, solid content was calculated | required by 150 degreeC 20 minute baking residue.
[実施例22~42、比較例8~10]
(正極の作製)
実施例1~21および比較例1、3、5で得られた樹脂微粒子水分散体の固形分100部に対して、それぞれ、正極活物質であるコバルト酸リチウム(LiCoO2)を4700部、アセチレンブラック100部、増粘剤としてカルボキシメチルセルロース100部を添加し、固形分50%になるようにイオン交換水を加えた後、混練して非水系二次電池電極用バインダー組成物を調製した。
さらに、この非水系二次電池電極用バインダー組成物を、それぞれ、集電体となる厚さ20μmのアルミ箔上にドクターブレードを用いて塗布した後、減圧加熱乾燥し、ロールプレスによる圧延処理を行い、厚さ50μmの正極合剤層を有する正極を作製した。
このようにして、実施例1~21および比較例1、3、5で得られた樹脂微粒子水分散体を用いて得られた正極用バインダー組成物および正極を、それぞれ実施例22~42、比較例8~10に係る正極用バインダー組成物および正極とした。 <Preparation of binder composition for non-aqueous secondary battery electrode and non-aqueous secondary battery electrode>
[Examples 22 to 42, Comparative Examples 8 to 10]
(Preparation of positive electrode)
4700 parts of lithium cobaltate (LiCoO 2 ), which is a positive electrode active material, and acetylene for 100 parts of the solid content of the resin fine particle aqueous dispersions obtained in Examples 1 to 21 and Comparative Examples 1, 3, and 5, respectively. 100 parts of black and 100 parts of carboxymethylcellulose as a thickener were added, ion-exchanged water was added so as to have a solid content of 50%, and kneaded to prepare a binder composition for a non-aqueous secondary battery electrode.
Furthermore, each non-aqueous secondary battery electrode binder composition was applied onto a 20 μm thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a positive electrode having a positive electrode mixture layer having a thickness of 50 μm was produced.
Thus, the positive electrode binder composition and the positive electrode obtained using the resin fine particle aqueous dispersions obtained in Examples 1 to 21 and Comparative Examples 1, 3, and 5 were compared with Examples 22 to 42, respectively. A positive electrode binder composition and a positive electrode according to Examples 8 to 10 were obtained.
実施例1~21および比較例1、3、5で得られた樹脂微粒子水分散体の固形分100部に対して、それぞれ、負極活物質としてメソフェーズカーボン(MCMB 6-28、平均粒径5~7μm、比表面積4m2/g大阪ガスケミカル社製)4800部、アセチレンブラック100部を添加し、固形分50%になるようにイオン交換水を加えた後、混練して非水系二次電池電極用バインダー組成物を調製した。
さらに、この非水系二次電池電極用バインダー組成物を、それぞれ、集電体となる厚さ20μmのアルミ箔上にドクターブレードを用いて塗布した後、減圧加熱乾燥し、ロールプレスによる圧延処理を行い、厚さ50μmの負極合剤層を有する負極を作製した。
このようにして、実施例1~21および比較例1、3、5で得られた樹脂微粒子水分散体を用いて得られた負極用バインダー組成物および負極を、それぞれ実施例22~42、比較例8~10に係る負極用バインダー組成物および負極とした。 (Preparation of negative electrode)
Mesophase carbon (MCMB 6-28, average particle size 5 to 5) was used as the negative electrode active material with respect to 100 parts of the solid content of the resin fine particle aqueous dispersions obtained in Examples 1 to 21 and Comparative Examples 1, 3, and 5. 7 μm, specific surface area 4 m 2 / g Osaka Gas Chemical Co., Ltd.) 4800 parts, 100 parts of acetylene black were added, ion-exchanged water was added to a solid content of 50%, and then kneaded to prepare a non-aqueous secondary battery electrode A binder composition was prepared.
Furthermore, each non-aqueous secondary battery electrode binder composition was applied onto a 20 μm thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a negative electrode having a negative electrode mixture layer having a thickness of 50 μm was produced.
In this way, the negative electrode binder compositions and negative electrodes obtained using the resin fine particle aqueous dispersions obtained in Examples 1 to 21 and Comparative Examples 1, 3, and 5 were compared with Examples 22 to 42, respectively. Negative electrode binder compositions and negative electrodes according to Examples 8 to 10 were obtained.
(正極の作製)
表3に示す組成によって得られた樹脂微粒子水分散体の固形分100部に対して、それぞれ、正極活物質であるコバルト酸リチウム(LiCoO2)を4700部、アセチレンブラック100部、増粘剤としてカルボキシメチルセルロース100部を加え、固形分50%になるようにイオン交換水を加えた後、混練して非水系二次電池電極用バインダー組成物を調製した。
さらに、この非水系二次電池電極用バインダー組成物を、それぞれ、集電体となる厚さ20μmのアルミ箔上にドクターブレードを用いて塗布した後、減圧加熱乾燥し、ロールプレスによる圧延処理を行い、厚さ50μmの正極合剤層を有する正極を作製した。
このようにして、表3に示す組成によって得られた樹脂微粒子水分散体を用いて得られた正極用バインダー組成物および正極を、それぞれ実施例43~65に係る正極用バインダー組成物および正極とした。 [Examples 43 to 65]
(Preparation of positive electrode)
As a solid content of 100 parts of the resin fine particle aqueous dispersion obtained by the composition shown in Table 3, 4700 parts of lithium cobaltate (LiCoO 2 ) as a positive electrode active material, 100 parts of acetylene black, and a thickener, respectively. After adding 100 parts of carboxymethyl cellulose and adding ion-exchanged water so as to have a solid content of 50%, the mixture was kneaded to prepare a binder composition for a non-aqueous secondary battery electrode.
Furthermore, each non-aqueous secondary battery electrode binder composition was applied onto a 20 μm thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a positive electrode having a positive electrode mixture layer having a thickness of 50 μm was produced.
Thus, the positive electrode binder composition and the positive electrode obtained using the resin fine particle aqueous dispersion obtained by the composition shown in Table 3 were used as the positive electrode binder composition and the positive electrode according to Examples 43 to 65, respectively. did.
表3に示す組成によって得られた樹脂微粒子水分散体の固形分100部に対して、それぞれ、負極活物質としてメソフェーズカーボン(MCMB 6-28、平均粒径5~7μm、比表面積4m2/g大阪ガスケミカル社製)4800部、アセチレンブラック100部を添加し、固形分50%になるようにイオン交換水を加えた後、混練して非水系二次電池電極用バインダー組成物を調製した。
さらに、この非水系二次電池電極用バインダー組成物を、それぞれ、集電体となる厚さ20μmのアルミ箔上にドクターブレードを用いて塗布した後、減圧加熱乾燥し、ロールプレスによる圧延処理を行い、厚さ50μmの負極合剤層を有する負極を作製した。
このようにして、表3に示す組成によって得られた樹脂微粒子水分散体を用いて得られた負極用バインダー組成物および負極を、それぞれ実施例43~65に係る負極用バインダー組成物および負極とした。 (Preparation of negative electrode)
With respect to 100 parts of the solid content of the resin fine particle aqueous dispersion obtained by the composition shown in Table 3, mesophase carbon (MCMB 6-28, average particle size 5 to 7 μm, specific surface area 4 m 2 / g as a negative electrode active material, respectively. 4800 parts of Osaka Gas Chemical Co., Ltd.) and 100 parts of acetylene black were added, ion-exchanged water was added so as to have a solid content of 50%, and kneaded to prepare a binder composition for a non-aqueous secondary battery electrode.
Furthermore, each non-aqueous secondary battery electrode binder composition was applied onto a 20 μm thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a negative electrode having a negative electrode mixture layer having a thickness of 50 μm was produced.
Thus, the negative electrode binder composition and the negative electrode obtained using the resin fine particle aqueous dispersion obtained by the composition shown in Table 3 were used as the negative electrode binder composition and the negative electrode according to Examples 43 to 65, respectively. did.
エポキシ樹脂;(製品名アデカレジンEM-1-60L、株式会社ADEKA製、エポキシ当量320、ビスフェノールA-エピクロロヒドリン型エポキシ樹脂)
1,4-ビス(ヒドロキシメチル)シクロヘキサン;(和光純薬工業株式会社製)
オキサゾリン基含有アクリル・スチレン樹脂;(製品名エポクロスK-2020E、株式会社日本触媒製、オキサゾリン当量550)
アミキュアVDH;(味の素ファインテクノ社製)
カルボジライトV-02;カルボジイミド硬化剤(日清紡績株式会社製、NCN当量600)
ポリアミド樹脂;共重合ポリアミド樹脂(製品名Griltex D1500A Suspension、エムスケミー・ジャパン株式会社製) In addition, the description of the product name in Table 3 is as follows.
Epoxy resin; (Product name Adeka Resin EM-1-60L, manufactured by ADEKA Corporation, epoxy equivalent 320, bisphenol A-epichlorohydrin type epoxy resin)
1,4-bis (hydroxymethyl) cyclohexane; (Wako Pure Chemical Industries, Ltd.)
Oxazoline group-containing acrylic / styrene resin; (product name Epocros K-2020E, manufactured by Nippon Shokubai Co., Ltd., oxazoline equivalent 550)
Amicure VDH; (Ajinomoto Fine Techno Co., Ltd.)
Carbodilite V-02; Carbodiimide curing agent (Nisshinbo Co., Ltd., NCN equivalent 600)
Polyamide resin; copolymerized polyamide resin (product name Gritex D1500A Suspension, manufactured by EMS Chemie Japan Co., Ltd.)
(正極の作製)
比較例5で得られた樹脂微粒子水分散体、比較例6、7で得られた共重合体溶液の固形分100部に対して、それぞれ、正極活物質であるコバルト酸リチウム(LiCoO2)を4700部、アセチレンブラック100部、増粘剤としてカルボキシメチルセルロース100部(さらに、比較例5で得られた樹脂微粒子水分散体には3官能エポキシ樹脂[製品名デナコールEX321、ナガセケムテックス(株)製]を30部、比較例6で得られた共重合体溶液には3官能エポキシ樹脂[デナコールEX321]を50部、比較例7で得られた共重合体溶液にはジアミノジフェニルエーテル[DPE/ODA、和歌山精化工業(株)製]を50部)、トルエンに溶解させたものを加えて、最終的にバインダー組成物の固形分が50%になるように調整し、混練して非水系二次電池電極用バインダー組成物を調製した。
さらに、この非水系二次電池電極用バインダー組成物を、それぞれ、集電体となる厚さ20μmのアルミ箔上にドクターブレードを用いて塗布した後、減圧加熱乾燥し、ロールプレスによる圧延処理を行い、厚さ50μmの正極合剤層を有する正極を作製した。
このようにして、比較例5で得られた樹脂微粒子水分散体、比較例6、7で得られた共重合体溶液を用いて得られた正極用バインダー組成物および正極を、それぞれ比較例11~13に係る正極用バインダー組成物および正極とした。 [Comparative Examples 11, 12, 13]
(Preparation of positive electrode)
Lithium cobaltate (LiCoO 2 ), which is a positive electrode active material, was added to 100 parts of the solid content of the resin fine particle aqueous dispersion obtained in Comparative Example 5 and the copolymer solution obtained in Comparative Examples 6 and 7, respectively. 4700 parts, acetylene black 100 parts, carboxymethyl cellulose 100 parts as a thickener (Furthermore, the resin fine particle aqueous dispersion obtained in Comparative Example 5 is a trifunctional epoxy resin [product name Denacol EX321, manufactured by Nagase ChemteX Corporation] ] In 30 parts, the copolymer solution obtained in Comparative Example 6 with 50 parts of trifunctional epoxy resin [Denacol EX321], and the copolymer solution obtained in Comparative Example 7 with diaminodiphenyl ether [DPE / ODA, 50 parts of Wakayama Seika Kogyo Co., Ltd.), and what is dissolved in toluene, the final solid content of the binder composition is 50% It was adjusted to and kneaded to a nonaqueous secondary battery electrode binder composition was prepared.
Furthermore, each non-aqueous secondary battery electrode binder composition was applied onto a 20 μm thick aluminum foil serving as a current collector using a doctor blade, dried by heating under reduced pressure, and subjected to a rolling process using a roll press. Then, a positive electrode having a positive electrode mixture layer having a thickness of 50 μm was produced.
Thus, the positive electrode binder composition and the positive electrode obtained using the resin fine particle aqueous dispersion obtained in Comparative Example 5 and the copolymer solution obtained in Comparative Examples 6 and 7, respectively, were used as Comparative Example 11. A positive electrode binder composition and a positive electrode according to -13.
比較例5で得られた樹脂微粒子水分散体、比較例6、7で得られた共重合体溶液の固形分100部に対して、それぞれ、負極活物質としてメソフェーズカーボン(MCMB 6-28、平均粒径5~7μm、比表面積4m2/g大阪ガスケミカル社製)4800部、アセチレンブラック100部(さらに、比較例5で得られた樹脂微粒子水分散体には3官能エポキシ樹脂[製品名デナコールEX321、ナガセケムテックス(株)製]を30部、比較例6で得られた共重合体溶液には3官能エポキシ樹脂[デナコールEX321]を50部、比較例7で得られた共重合体溶液にはジアミノジフェニルエーテル[DPE/ODA、和歌山精化工業(株)製]を50部)、トルエンに溶解させたものを加えて最終的にバインダー組成物の固形分が50%になるように調整し、混練して非水系二次電池電極用バインダー組成物を調製した。
さらに、この非水系二次電池電極用バインダー組成物を、それぞれ、集電体となる厚さ20μmのアルミ箔上にドクターブレードを用いて塗布した後、減圧加熱乾燥し、ロールプレスによる圧延処理を行い、厚さ50μmの負極合剤層を有する負極を作製した。
このようにして、比較例5で得られた樹脂微粒子水分散体、比較例6、7で得られた共重合体溶液を用いて得られた負極用バインダー組成物および負極を、それぞれ比較例11~13に係る負極用バインダー組成物および負極とした。 (Preparation of negative electrode)
With respect to 100 parts of the solid content of the resin fine particle aqueous dispersion obtained in Comparative Example 5 and the copolymer solution obtained in Comparative Examples 6 and 7, mesophase carbon (MCMB 6-28, average) was used as the negative electrode active material, respectively. Particle size 5-7 μm, specific surface area 4 m 2 / g Osaka Gas Chemical Co., Ltd. 4800 parts, acetylene black 100 parts (Furthermore, the resin fine particle aqueous dispersion obtained in Comparative Example 5 contains trifunctional epoxy resin [product name Denacol] 30 parts of EX321, manufactured by Nagase ChemteX Corp., 50 parts of the trifunctional epoxy resin [Denacol EX321] in the copolymer solution obtained in Comparative Example 6, and the copolymer solution obtained in Comparative Example 7 In addition, 50 parts of diaminodiphenyl ether [DPE / ODA, manufactured by Wakayama Seika Kogyo Co., Ltd.], dissolved in toluene, and finally the solid content of the binder composition is It was adjusted to 0%, and the kneaded nonaqueous secondary battery electrode binder composition was prepared.
Furthermore, each non-aqueous secondary battery electrode binder composition was applied onto a 20 μm thick aluminum foil serving as a current collector using a doctor blade, and then dried by heating under reduced pressure, followed by rolling by a roll press. Then, a negative electrode having a negative electrode mixture layer having a thickness of 50 μm was produced.
Thus, the resin fine particle water dispersion obtained in Comparative Example 5 and the negative electrode binder composition and negative electrode obtained using the copolymer solutions obtained in Comparative Examples 6 and 7 were respectively compared with Comparative Example 11. A negative electrode binder composition and a negative electrode according to 13 to 13.
先に作製した正極(実施例22~42、比較例8~10、実施例43~65、比較例11~13)を、直径9mmに打ち抜き作用極とし、金属リチウム箔(厚さ0.15mm)を対極として、作用極および対極の間に多孔質ポリプロピレンフィルムからなるセパレーター(セルガード社製 #2400)を挿入積層し、電解液(エチレンカーボネートとジエチルカーボネートを1:1に混合した混合溶媒にLiPF6を1Mの濃度で溶解させた非水電解液)を満たして二極密閉式金属セル(宝仙社製HSフラットセル)を組み立てた。セルの組み立てはアルゴンガス置換したグローボックス内で行い、セル組み立て後、所定の電池特性評価を行った。 <Assembly of lithium secondary battery “positive electrode” evaluation cell>
The previously produced positive electrodes (Examples 22 to 42, Comparative Examples 8 to 10, Examples 43 to 65, and Comparative Examples 11 to 13) were punched into a diameter of 9 mm and used as a metal lithium foil (thickness 0.15 mm). As a counter electrode, a separator (# 2400 manufactured by Celgard Co., Ltd.) made of a porous polypropylene film is inserted and laminated between the working electrode and the counter electrode, and LiPF 6 in a mixed solvent in which ethylene carbonate and diethyl carbonate are mixed 1: 1. Was filled with a non-aqueous electrolyte solution having a concentration of 1 M), and a two-pole sealed metal cell (HS flat cell manufactured by Hosensha) was assembled. The cell was assembled in a glow box substituted with argon gas, and after the cell was assembled, predetermined battery characteristics were evaluated.
先に作製した負極(実施例22~42、比較例8~10、実施例43~65、比較例11~13)を、直径9mmに打ち抜き作用極とし、金属リチウム箔(厚さ0.15mm)を対極として、作用極および対極の間に多孔質ポリプロピレンフィルムからなるセパレーター(セルガード社製 #2400)を挿入積層し、電解液(エチレンカーボネートとジエチルカーボネートを1:1に混合した混合溶媒にLiPF6を1Mの濃度で溶解させた非水電解液)を満たして二極密閉式金属セル(宝仙社製HSフラットセル)を組み立てた。セルの組み立てはアルゴンガス置換したグローボックス内で行い、セル組み立て後、所定の電池特性評価を行った。 <Assembly of lithium secondary battery “negative electrode” evaluation cell>
The previously prepared negative electrodes (Examples 22 to 42, Comparative Examples 8 to 10, Examples 43 to 65, and Comparative Examples 11 to 13) were punched into a diameter of 9 mm and used as a metal lithium foil (thickness 0.15 mm). As a counter electrode, a separator (# 2400 manufactured by Celgard Co., Ltd.) made of a porous polypropylene film is inserted and laminated between the working electrode and the counter electrode, and an electrolyte solution (LiPF 6 in a mixed solvent in which ethylene carbonate and diethyl carbonate are mixed 1: 1). Was filled with a non-aqueous electrolyte solution having a concentration of 1 M), and a two-pole sealed metal cell (HS flat cell manufactured by Hosensha) was assembled. The cell was assembled in a glow box substituted with argon gas, and after the cell was assembled, predetermined battery characteristics were evaluated.
上記の方法で得られたリチウムイオン二次電池電極(正極および負極)を用いて結着性および耐電解液性を評価し、リチウムイオン二次電池電極(正極および負極)評価用セルを用いて電池特性を評価した。 <Assembly of lithium secondary battery “positive electrode” evaluation cell>
The lithium ion secondary battery electrode (positive electrode and negative electrode) obtained by the above method was used to evaluate the binding property and the electrolytic solution resistance, and the lithium ion secondary battery electrode (positive electrode and negative electrode) evaluation cell was used. Battery characteristics were evaluated.
各リチウムイオン二次電池電極の表面にナイフを用いて、合剤層から集電体に達する深さまでの切込みを2mm間隔で縦横それぞれ6本入れて碁盤目の切込みを入れた。この切り込みに粘着テープを貼り付けて直ちに引き剥がし、活物質の脱落の程度を目視判定で判定した。評価基準を下記に示す。評価結果を表4に示す。
○ :「剥離なし」
○△:「わずかに剥離(実用上問題のないレベル)」
△×:「ほとんどの部分で剥離」
× :「完全に剥離」 (Evaluation of binding properties)
Using a knife on the surface of each lithium ion secondary battery electrode, 6 incisions were made from the mixture layer to the depth reaching the current collector, both vertically and horizontally, at 2 mm intervals to make a grid cut. An adhesive tape was applied to the cut and immediately peeled off, and the degree of the active material falling off was determined by visual judgment. The evaluation criteria are shown below. The evaluation results are shown in Table 4.
○: “No peeling”
○ △: “Slightly peeled off (a level where there is no practical problem)”
△ ×: “Peeling at most parts”
×: “Completely peeled”
各リチウムイオン二次電池電極をプロピレンカーボネート液に70℃、24時間浸漬し、浸漬前後での膜の膨潤状態、樹脂の溶出状態を下記の通り算出し、比較評価した。
膨潤率(%)=(浸漬後重量)/(浸漬前重量)
溶出率(%)=(浸漬乾燥後重量)/(浸漬前重量)-1
膨潤率はその値が100%に近いほど、溶出率は0%に近いほど耐電解液性が高いことを示す。評価結果を表4に示す。 (Evaluation of electrolyte resistance)
Each lithium ion secondary battery electrode was immersed in a propylene carbonate solution at 70 ° C. for 24 hours, and the swelling state of the film and the elution state of the resin before and after the immersion were calculated as follows and subjected to comparative evaluation.
Swelling ratio (%) = (weight after immersion) / (weight before immersion)
Dissolution rate (%) = (weight after immersion drying) / (weight before immersion) −1
As the swelling rate is closer to 100% and the dissolution rate is closer to 0%, the resistance to electrolytic solution is higher. The evaluation results are shown in Table 4.
各リチウムイオン二次電池電極評価用セルの充放電サイクル試験を行った。1回目の放電容量を100%として70℃、100時間後の放電容量を測定し変化率とした(100%に近いほど良好であることを示す)。評価結果を表4に示す。 (Evaluation of battery characteristics)
A charge / discharge cycle test was conducted on each lithium ion secondary battery electrode evaluation cell. The discharge capacity at the first time was set to 100%, and the discharge capacity after 100 hours at 70 ° C. was measured to determine the rate of change (the closer to 100%, the better). The evaluation results are shown in Table 4.
Claims (6)
- 官能基含有架橋型樹脂微粒子を含む非水系二次電池電極用バインダー組成物であって、
官能基含有架橋型樹脂微粒子が、
(A)1分子中に1つのエチレン性不飽和基と、単官能または多官能エポキシ基とを有する単量体(a)、1分子中に1つのエチレン性不飽和基と、単官能または多官能アミド基とを有する単量体(b)、および1分子中に1つのエチレン性不飽和基と、単官能または多官能水酸基とを有する単量体(c)からなる群より選ばれる少なくとも1つの単量体0.1~20重量%、
(B)1分子中に1つのエチレン性不飽和基と、単官能または多官能アルコキシシリル基とを有する単量体(d)、および1分子中に2つ以上のエチレン性不飽和基を有する単量体(e)からなる群より選ばれる少なくとも1つの単量体0.1~5重量%、および、
(C)前記単量体(a)~(e)以外の、エチレン性不飽和基を有する単量体(k)75~99.8重量%
を含むエチレン性不飽和基を有する単量体を水中にて界面活性剤の存在下、ラジカル重合開始剤によって乳化重合してなる樹脂微粒子であることを特徴とする、非水系二次電池電極用バインダー組成物。 A binder composition for a non-aqueous secondary battery electrode containing functional group-containing crosslinked resin fine particles,
Functional group-containing crosslinked resin fine particles
(A) Monomer having one ethylenically unsaturated group and monofunctional or polyfunctional epoxy group in one molecule (a) One ethylenically unsaturated group in one molecule and monofunctional or polyfunctional At least one selected from the group consisting of a monomer (b) having a functional amide group and a monomer (c) having one ethylenically unsaturated group and a monofunctional or polyfunctional hydroxyl group in one molecule. 0.1-20% by weight of one monomer,
(B) a monomer (d) having one ethylenically unsaturated group and a monofunctional or polyfunctional alkoxysilyl group in one molecule, and two or more ethylenically unsaturated groups in one molecule 0.1 to 5% by weight of at least one monomer selected from the group consisting of monomers (e), and
(C) Monomers having an ethylenically unsaturated group other than the monomers (a) to (e) (k) 75 to 99.8% by weight
Non-aqueous secondary battery electrode, characterized in that it is a resin fine particle obtained by emulsion polymerization of a monomer having an ethylenically unsaturated group containing water with a radical polymerization initiator in the presence of a surfactant in water Binder composition. - エチレン性不飽和基を有する単量体(k)が、1分子中に1つのエチレン性不飽和基と、炭素数8~18のアルキル基とを有する単量体(m)および/または1分子中に1つのエチレン性不飽和基と、環状構造とを有する単量体(n)を少なくとも含み、該単量体(m)および(n)が、エチレン性不飽和基を有する単量体全体((a)~(e)および(k))中に合計で30~95重量%含まれることを特徴とする、請求項1記載の非水系二次電池電極用バインダー組成物。 The monomer (k) having an ethylenically unsaturated group and the monomer (m) having one ethylenically unsaturated group and an alkyl group having 8 to 18 carbon atoms in one molecule and / or one molecule A monomer (n) having at least one ethylenically unsaturated group and a cyclic structure, wherein the monomers (m) and (n) are all monomers having an ethylenically unsaturated group The binder composition for a non-aqueous secondary battery electrode according to claim 1, wherein the binder composition is contained in a total amount of 30 to 95% by weight in ((a) to (e) and (k)).
- 未架橋のエポキシ基含有化合物、未架橋のアミド基含有化合物、未架橋の水酸基含有化合物、および未架橋のオキサゾリン基含有化合物からなる群より選ばれる少なくとも1つの未架橋の化合物(D)を含むことを特徴とする、請求項1または2記載の非水系二次電池電極用バインダー組成物。 Including at least one uncrosslinked compound (D) selected from the group consisting of an uncrosslinked epoxy group-containing compound, an uncrosslinked amide group-containing compound, an uncrosslinked hydroxyl group-containing compound, and an uncrosslinked oxazoline group-containing compound. The binder composition for nonaqueous secondary battery electrodes according to claim 1 or 2, wherein
- 請求項1~3いずれか記載の非水系二次電池電極用バインダー組成物を用いてなることを特徴とする、非水系二次電池電極。 A nonaqueous secondary battery electrode comprising the binder composition for a nonaqueous secondary battery electrode according to any one of claims 1 to 3.
- 請求項4記載の非水系二次電池電極を用いてなることを特徴とする、非水系二次電池。 A non-aqueous secondary battery comprising the non-aqueous secondary battery electrode according to claim 4.
- リチウムイオン二次電池であることを特徴とする、請求項5記載の非水系二次電池。 The non-aqueous secondary battery according to claim 5, wherein the non-aqueous secondary battery is a lithium ion secondary battery.
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Also Published As
Publication number | Publication date |
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CN102439769A (en) | 2012-05-02 |
US20120095131A1 (en) | 2012-04-19 |
JP5449327B2 (en) | 2014-03-19 |
KR20120027189A (en) | 2012-03-21 |
US9905855B2 (en) | 2018-02-27 |
KR101698623B1 (en) | 2017-01-20 |
JPWO2010114119A1 (en) | 2012-10-11 |
CN102439769B (en) | 2014-10-08 |
US20160156039A1 (en) | 2016-06-02 |
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